5-(Tert-butoxycarbonylamino)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxylic acid → 5-amino-N-[5-(4-amino-5-methoxy-azepan-1-yl)-1-methyl-pyrazol-4-yl]-2-(3-fluoro-2-pyridyl)thiazole-4-carboxamide

HRID 1915911Notes

Reaction equation

HRID 1915911 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH3:24])[C:6]=1[N:7]1[CH2:13][CH2:12][C@@H:11]([O:14][CH3:15])[C@H:10]([NH:16]C(=O)OC(C)(C)C)[CH2:9][CH2:8]1.C(OC([NH:32][C:33]1[S:37][C:36]([C:38]2[C:43]([F:44])=[CH:42][CH:41]=[CH:40][N:39]=2)=[N:35][C:34]=1[C:45](O)=[O:46])=O)(C)(C)C>>[NH2:32][C:33]1[S:37][C:36]([C:38]2[C:43]([F:44])=[CH:42][CH:41]=[CH:40][N:39]=2)=[N:35][C:34]=1[C:45]([NH:1][C:2]1[CH:3]=[N:4][N:5]([CH3:24])[C:6]=1[N:7]1[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH:10]([NH2:16])[CH2:9][CH2:8]1)=[O:46]

Participants

3

Reactant 2

HCID 698113535-(Tert-butoxycarbonylamino)-2-(3-fluoropyridin-2-yl)thiazole-4-carboxylic acidHCID 86680114tert-butyl ((4R,5R)-1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-methoxyazepan-4-yl)carbamate

Product 1

HCID 749831925-amino-N-[5-(4-amino-5-methoxy-azepan-1-yl)-1-methyl-pyrazol-4-yl]-2-(3-fluoro-2-pyridyl)thiazole-4-carboxamide

Procedure

Following the procedure Example 101, reacting tert-butyl ((4R,5R)-1-(4-amino-1-methyl-1H-pyrazol-5-yl)-5-methoxyazepan-4-yl)carbamate and 5-((tert-butoxycarbonyl)amino)-2-(3-fluoro-pyridin-2-yl)thiazole-4-carboxylic acid gave racemic 323 (35.8 mg, 24% over two steps). 1H NMR (400 MHz, DMSO) δ 8.84 (s, 1H), 8.43 (d, J=4.6 Hz, 1H), 7.89-7.78 (m, 1H), 7.66 (s, 2H), 7.62 (s, 1H), 7.48 (dt, J=8.3, 4.1 Hz, 1H), 3.65 (s, 3H), 3.28 (d, J=7.5 Hz, 5H), 3.26-2.95 (m, 8H), 2.07 (dd, J=10.6, 4.4 Hz, 1H), 1.92 (dd, J=10.6, 7.4 Hz, 1H), 1.79-1.55 (m, 2H). LCMS (ES+) m/z 461 (M+1)

Workup

  1. customgave racemic 323 (35.8 mg, 24% over two steps)

Sources & evidence

ORD record
ord-106b1299f8354b768f5a75031456856b
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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